19158-51-1 | Tosyl cyanide

Packsize	Purity	Availability	Price	Discounted Price
1g	95%	in stock	$24.00	$17.00
5g	95%	in stock	$53.00	$37.00
25g	95%	in stock	$242.00	$170.00

Description

• Catalog Number: AB13001
• Chemical Name: Tosyl cyanide
• CAS Number: 19158-51-1
• Molecular Formula: C8H7NO2S
• Molecular Weight: 181.2117
• MDL Number: MFCD00009977
• SMILES: N#CS(=O)(=O)c1ccc(cc1)C

Computed Properties

• Complexity: 285
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 12
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• XLogP3: 2.3

Upstream Synthesis Route

p-Toluenesulfonyl cyanide, also known as Tosyl cyanide, is a versatile reagent widely used in chemical synthesis. Its unique structure and reactivity make it a valuable tool in various organic transformations.1. Nitrile Synthesis: p-Toluenesulfonyl cyanide can be employed for the synthesis of nitriles from primary and secondary amines. By reacting with amines under suitable conditions, Tosyl cyanide facilitates the conversion of the amino group into a nitrile functionality. This process is particularly useful in the preparation of pharmaceutical intermediates and fine chemicals.2. Nucleophilic Cyanation: Tosyl cyanide serves as a cyanating agent in the presence of nucleophiles such as Grignard reagents or organolithium compounds. The reactivity of the cyanide group allows for the introduction of the cyanide moiety into various carbon-based molecules, enabling the formation of complex organic structures.3. Isocyanide Synthesis: Through a rearrangement process known as the Curtius Rearrangement, p-Toluenesulfonyl cyanide can be converted into isocyanides. Isocyanides are versatile building blocks in organic synthesis, participating in a wide range of reactions to produce diverse chemical motifs.4. Oxidative Functionalization: Tosyl cyanide can also act as a mild oxidizing agent, facilitating oxidative functionalization reactions in the presence of suitable catalysts. This allows for the generation of valuable functional groups within organic molecules with high efficiency and selectivity.In summary, p-Toluenesulfonyl cyanide finds extensive application in the synthesis of nitriles, nucleophilic cyanation, isocyanide synthesis, and oxidative functionalization reactions. Its versatile reactivity and compatibility with various organic functionalities make it a valuable reagent in modern organic chemistry.

Literature

• Photochemically induced radical transformation of C(sp3)-H bonds to C(sp3)-CN bonds.

  Organic letters 20111104

• Click azide-nitrile cycloaddition as a new ligation tool for the synthesis of tetrazole-tethered C-glycosyl alpha-amino acids.

  The Journal of organic chemistry 20081219

• Mild cobalt-catalyzed hydrocyanation of olefins with tosyl cyanide.

  Angewandte Chemie (International ed. in English) 20070101

• Synthesis of 3-substituted bicyclic imidazo[1,2-d][1,2,4]thiadiazoles and tricyclic benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazoles.

  The Journal of organic chemistry 20050805

• 2-azabicyclo[2.2.2]octa-3,5-dione via a nitrile Diels-Alder reaction.

  The Journal of organic chemistry 20031017